


Truth Or Dare

by lostinmymindforever



Category: Supernatural
Genre: F/F, F/M, First Time, Foursome - F/F/M/M, Foursome - M/M/M/M, Genderswap, M/M, girl!Gabriel, girl!castiel
Language: English
Status: Completed
Published: 2013-02-26
Updated: 2013-02-26
Packaged: 2017-12-03 16:30:28
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,089
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/700336
Author URL: https://archiveofourown.org/users/lostinmymindforever/pseuds/lostinmymindforever
Summary: <blockquote class="userstuff">
              <p>Sam and Dean don’t know it, but they weren’t in their 20s when they met their first angels, when they met Castiel and Gabriel for the very first time. Of course, Gabriel and Castiel looked quite different in those days.</p>
            </blockquote>





	Truth Or Dare

**Author's Note:**

> Written for my friend Anna over on Tumblr who was having a bad day today  
> Sam is 14, Dean is 18

Sam and Dean don’t know it, but they weren’t in their 20s when they met their first angels, when they met Castiel and Gabriel for the very first time. Of course, Gabriel and Castiel looked quite different in those days.

Sam was 14, the new kid yet again and Dean was 18, working a part time job to earn money to support the two of them. Dean had come home from work to the sound of giggling coming from the kitchen. Sam was sitting at the kitchen table, his books spread out on the table, two girls a bit older than him sitting on either side of him. 

“So who are your friends, Sammy?” Dean had asked, leaning against the doorframe.

Sam had blushed a little, “This is Gabby,” he pointed to the blonde girl who was leaning very close to him, “and this is her sister, Cassie,” at that he motioned to the brunette sitting on the opposite side of him. “They are helping me with my homework."

The girls were night and day. Gabby was wearing one of the skimpiest outfits Dean had seen on anyone in real life to that point, and Cassie had this bookish, almost librarian looking outfit on. Both girls were beautiful, Dean had to admit that, and Dean was a bit jealous at the attention the two of them seemed to be lavishing onto his baby brother.

Dean greeted each of them and grabbed a drink from the fridge, sitting down in the only open seat at the table. He watched as Gabby kept leaning in towards Sam, explaining questions he was having trouble with. Dean could see Sam kept sneaking glances at the girl’s cleavage, which was very much on display.

Cassie was biting her lip, giving Sam and Dean these little looks that Dean swore were her trying to flirt but being too shy to be more open about it. Sam was blushing almost constantly and Dean watched his eyes go wide within seconds of Gabby reaching down towards her lap, obviously it wasn’t her lap she had placed her hand on.

Dean watched them in silence for at least a half hour, watched Cassie’s innocent little looks and Gabby’s obvious flirtations. Sam stood to stretch at that point, homework done. Even though Sam was wearing too large pants Dean could see the obvious bulge in them and the turned away before his baby brother caught him perving. 

Dean wasn’t sure how the four of them ended up on the couch, but soon enough that’s where they were. It was a tight fit, Dean on one end, Sam on the other, the girls in between them.

Gabby grinned, her almost golden eyes flashing with mischief as she said, “We should play truth or dare.”

Dean was always up for that, he pretty much had no shame and would do just about anything on a dare. Sam nodded, biting his lip, and Dean knew that his brother hoped that the girls wouldn’t dare him to do anything too outlandish.

They moved the coffee table, the four of them sitting on the floor in a small circle. Dean had raided their father’s alcohol supply for forfeits, knowing damn well he could replace whatever they drank before his dad got back from his most recent of hunts. They were seated boy girl boy girl, with Sam and Dean across from each other and the girls across from each other.

Gabby started, as the game was her idea. She looked at Sam, voice almost a purr as she asked, “Truth or Dare, Sammy?”

Sam swallowed, not wanting to do a dare on his first turn so he answered, “Truth.”

“Have you ever kissed a boy?”

Sam shook his head, “No.” He turned towards Cassie, “Truth or Dare.”

“Truth.”

“Who was your first kiss?”

She blushed, looking down at her hands, “Gabby.”

Dean and Sam both blinked in shock at that revelation. 

“Dean, Truth or Dare?”

“Truth.”

“Have you ever had sex with a guy?”

“Not yet.” Dean quickly turned towards Gabby, “Truth or Dare?”

Gabby looked like she was thinking it over, before leaning in and saying in a seductive voice, “Dare.”

“Fuck,” Dean said under his breath, clearing his throat before speaking again, “I dare you to kiss... Cassie.”

Gabby rolled her eyes, getting onto her knees and practically crawling over towards her sister. She reached up, gently pulling Cassie towards her, kissing her deeply, their tongues moving together. One of them moaned, but Sam and Dean weren’t quite sure which one had made the sound. By the time the girls pulled apart both Sam and Dean were hard, faces flushed with arousal.

“Fuck,” Sam and Dean said in almost unison, which caused Gabby and Cassie to giggle.

Gabby turned her attention to Dean, a smirk on her face, “Truth or Dare, Dean?”

“Dare,” Dean answered, hoping that the girls wouldn’t be too terrible to him and Sammy.

“Mm, kiss Sammy, on the lips.”

Sam sat still as Dean moved close to him, not only had Sam never kissed a guy before, he’d never kissed anyone. Dean could tell Sam was nervous, and whispered softly when he was close, “It’s okay, Sammy, I’ll take care of you.”

It wasn’t the most passionate of kisses, but Dean had to admit it was the hottest kiss he had ever taken part of. When Dean pulled away Sam let out a little moan of disappointment, and Dean could totally understand why. He hadn’t wanted to stop kissing Sammy, but he had to stop before things went too far.

“Sam? Truth or Dare?” Dean asked, voice a bit rough.

“Da... dare,” Sam answered with a blush. He knew Dean wouldn’t be too mean, at least he hoped not.

“I dare you to kiss Cassie.”

Sam grinned shyly, leaning over to kiss the girl. He let out a surprised moan when she grabbed him by the back of the head, holding him in place as they kissed. Sam was panting by the time she finally let him go and Cassie had this little grin on her face. Gabby let out a wolf whistle, winking at Sam.

“Damn Sammy, that was one hot kiss if the look on Cassie’s face is anything to go by,” the blonde said with a wink.

“Um... Cassie, Truth or Dare?”

Cassie seemed to think about how to answer for a second before grinning, “Truth.”

“Have you ever had sex?”

Cassie grinned, giving Gabby a heated look, “All the time.”

Both Dean and Sam’s eyes widened at that.

“Gabby, Truth or Dare, sweetie?”

“Truth?”

“Who was the last person you had sex with?”

Gabby grinned, licking her lips, “Mike, I rode him all night long last night.”

Sam and Dean weren’t sure who Mike was, but he was one lucky guy.

Gabby grinned, pouring each of them a shot, “Since no one is chickening out I say we have a little drink just for the hell of it.”

Dean shrugged, giving a ‘why the hell not’ look.

The four of them downed their shots, Sam wincing a bit as the liquor burned down his throat.

“It’s my turn again, isn’t it?” Gabby asked, grinning. 

Dean and Sam were learning that that grin meant that trouble might just be on the horizon, but were too involved in the game to fight it. 

She gave an innocent look, turning her attention to her sister, “Truth or Dare, Cassie?”

“Dare.”

“I dare you to suck Dean’s cock.”

Dean’s eyes widened as Cassie crawled towards him, looking up at him at the last moment to make sure he was okay with this. When he didn’t say no or push her away she quickly opened his jeans, pulling his hard cock out. With a grin she leaned forward, teasing the head of his cock with her tongue, before engulfing him in one quick movement.

Dean moaned as Cassie began to bob up and down the length of his cock, sucking him like a pro. Dean could tell this was far from the first blowjob she had given. He rested his hand on the back of her head, as she continued to work him fast and messy, until he was coming harder and faster than he had ever come before. His eyes had been on Sammy’s face, who was watching with his jaw dropped, pupils wide with lust.

Cassie pulled off of Dean with a wet pop, licking her lips. She turned towards Gabby, kissing her sister, sharing Dean’s flavor with the other girl before returning to her seat as if nothing had happened. 

Dean pulled his pants back up, grabbed the bottle and took a large drink before passing the bottle across to Sam who definitely looked like he needed a drink.

“Sam, Truth or Dare?” Cassie asked, as if she hadn’t just given his brother a blowjob not five feet in front of him.

“Truth,” as much as he wanted to answer dare, he wasn’t quite sure he could handle whatever the seemingly innocent looking girl was about to throw at him.

“Have you ever had a blowjob?”

Sam shook his head, answering softly, “No.”

Gabby raised an eyebrow at that, “You poor, poor boy. How could someone be so mean to deprive you of that?”

Sam shrugged, “Um, Dean.”

“Yeah, kiddo?”

“Truth or Dare?”

“Truth.”

“What’s the farthest you’ve gone with a guy?”

“Got a blowjob from a guy one time, and gave a handjob, never went all the way.”

“Fuck,” Sam whispered, taking another drink. 

Gabby held out her hand for the bottle, taking a nice long drink of it before passing it to Dean. The bottle made it’s way back to Sam before Dean took his turn asking.

Figuring that it would be fine to ask someone he had already asked he said, “Sammy, Truth or Dare?”

“Dare.”

“I dare you to kiss Gabby.”

Sam nodded, and within seconds the girl was on him, her legs straddling his lap as they kissed. He moaned into the kiss as she reached down between them, unzipped him pants, pulled out his cock and began stroking him as they kissed. He let out a whimper as she moved a bit, removing her hand from his cock, only to moan as she sank down onto him. It was obvious to everyone in that moment that Gabby wasn’t wearing any panties.

Gabby shoved Sammy down onto his back, moaning as she began to move up and down his cock, head thrown back as she rode him.

“Oh, fuck,” Dean whispered, eyes wide as he watched his baby brother losing his virginity in front of him. Dean didn’t know where to look as Cassie stood, stripping off her clothes before moving over to Sam and Gabby. She pulled Gabby’s shirt over her head, kissing her sister’s neck as she undid the girl’s bra, tossing it over her shoulder. Dean noticed that Gabby’s skirt opened on the side as Cassie undid the fastening, removing the fabric, tossing that also out of the way.

Dean was hard again, but wasn’t sure if he should get naked too or just sit and enjoy the show. He watched as Cassie yanked Sam’s pants and boxers down the rest of the way, Gabby shoving at Sam’s shirt, silently telling him to take it off.

“Knew you’d feel good in me, Sammy,” Gabby moaned, head thrown back in pleasure. 

Cassie was kneeling between Sam’s legs, arms around Gabby’s body, mouth kissing and sucking along her neck. She looked back at Dean with a grin, “You gonna get naked and join us or are you just gonna watch?”

Dean seemed to snap out of his daze at that, quickly undressing, crawling over to the tangle of limbs in front of him. 

Gabby ran her hand down Sam’s cheek, “You wanna take care of Dean, suck his cock for him? Or do you want him to fuck you?”

Dean could see Sam’s eyes widen, and let out a moan as Sam’s mouth opened, a moan of his own falling from his lips. Sam looked up at Dean then down to Dean’s very hard cock. “Want... fuck, want it all,” the words were a whisper, but Dean could feel a shock of arousal rush through him all the same.

He moved closer to Sam, running his fingers through his baby brother’s hair. Their eyes locked, and Dean knew in that moment that they would never go back to just being brothers, not after this night. Dean almost lost it when Sam’s tongue touched his cock, the innocent, unsure motion,the way Sam’s eyes closed with pleasure. He had to stop himself from thrusting into Sam’s mouth, and yet it was all he could think of in that moment.

When Sam’s lips closed around him, Dean gasped, eyes almost rolling back in his skull at the perfection of it. Sam moaned around his shaft and Dean looked over to see Cassie leaning down behind Gabby. 

“That’s it, Cassie, get Sam all nice and ready for Dean. Gonna be so hot watching Dean fuck him.”

Dean looked at Gabby, moaning as he asked, “You two plan this or something?”

Gabby laughed, still moving slowly up and down Sam’s cock, “Planned on seducing Sam, you, fuck, Sam that feels incredible, such a fast learner, you are a much welcome bonus.”

Dean didn’t want to pull out of Sam’s mouth, but knew he’d come again much too soon if he allowed his brother to keep sucking him. Sam was a natural, and had Dean not know that he was a virgin he would have asked just who he’d been practicing on. 

Sam gave a moan of loss when Dean pulled away, trying to get him back into his mouth, but Dean stayed out of reach.

“Cassie, why don’t let Dean finish prepping Sam and give Sam’s mouth something to play with?”

“Mm, yeah, I can do that,” Cassie whispered, crawling around until she was by Sam’s head, moving to straddle his face. She let out a moan as Sam began to explore her with his tongue, what he lacked in experience, he obviously made up for with enthusiasm. “Oh, fuck, Sam, right there,” she moaned as his tongue moved against her clit.

Dean moved between Sam’s spread legs, noticing a bottle of lube next to his thigh. “You brought lube?”

Gabby laughed, “A girl has always got to be prepared.”

Shaking his head Dean poured some of the slick liquid onto his fingers. He hadn’t done this before, but he knew he was a quick study, just like Sammy obviously was. When his fingers brushed against Sam’s hole they slid in easily, obviously that was what Cassie had been up to while Sam had been sucking Dean’s cock. Two fingers soon made way to three as Dean stretched and slicked up Sammy’s passage, Gabby’s wetness mixing with the lube.

Sammy’s whole body bucked up as Dean brushed something inside of him that obviously had Sam feeling really good. 

Gabby moaned loudly, her body clenching around Sam as he came inside of her, the feeling of his warm cum filling her up setting off her orgasm. Cassie let out a breathy little moan, tensing over Sam before she started shaking, moaning and cursing as she rode his face. Moments later both girls were on the floor on either side of Sam, watching with lust filled gazes as Dean slowly entered him. 

Dean had to stop himself from coming right away, no one he had ever fucked had felt as good as Sammy had. His brother’s body holding him tight. It was better than any other time had been, and part of Dean knew it was because it was Sammy he was fucking, Sammy the one person he loved more than anyone. He slowly began to move in and out of Sammy’s body, loving the breathy little moans Sam made as he moved. 

Dean could hear the girls moaning and looked over to see them locked in one hell of a hot 69, but he quickly returned his attention to his brother. As hot as the girls were, they were nothing compared to his sweet little Sammy.

“Dean, please, more,” Sam begged, reaching up to pull Dean down for a kiss.

It screwed up their angle, but neither of them cared as their tongues danced back and forth in each others mouths. Dean could taste a sweetness he knew was Cassie, but under that was a taste he knew without a doubt was pure unadulterated Sam. Dean knew damn well he was gonna be addicted to that taste.

He fucked Sam long and slow until Sam was trembling under him, his eyes rolling back as his orgasm ripped through him, covering their stomachs in his seed. That was all it took to send Dean over the edge, moaning and cursing as his cock began to spurt hot cum into Sam. Dean rolled them, still buried in Sam’s body, panting and smiling as he gently kissed his brother tenderly. He could hear the girls moaning loudly as they both came.

He wasn’t sure how long they had rested, but soon he found himself laying on his back, Sam next to him, the two of them kissing as Cassie slowly sunk down Sam’s cock and Gabby started riding him. Dean knew this had to be one the hottest things he had ever done in his life, and it was only made better by the fact that he was sharing it with Sam.

The four of the messed around for hours, each of them taking turns with each other, and around midnight the girls got dressed, grabbed their things and left Sam and Dean. Dean grinned at Sam, taking him by the hand and leading him into the bathroom. The two of them shared a hot shower, where they couldn’t keep their hands off of each other, before falling in bed together.

Sam and Dean never saw Cassie or Gabby again, not that they knew at any rate. But years later, after so much had happened, after Sam and Dean had broken up and gotten back together, after Dean made his deal and went to Hell, after Castiel had dragged him out, Gabriel at his side, they shared another night with another set of siblings so much like the two girls who they had known all those years earlier. And if Dean started to wonder if Castiel and Gabriel were Cassie and Gabby, well he kept that to himself.


End file.
